


Straight to Hell

by crowleyhasfeels



Series: The Babysitter Chronicles [1]
Category: Supernatural
Genre: Babysitting, Blow Jobs, M/M, Older Castiel, Oral Sex, Underage Dean, Underage Sex
Language: English
Status: Completed
Published: 2016-10-16
Updated: 2016-10-16
Packaged: 2018-08-22 17:07:41
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 2,170
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8293439
Author URL: https://archiveofourown.org/users/crowleyhasfeels/pseuds/crowleyhasfeels
Summary: Dean gets asked to babysit for Castiel while he goes on a date. After Castiel's date goes wrong, Dean tries to show him how it was her loss.





	

**Author's Note:**

> There is underage sexual activity in this. If this bugs you, please stop now!!

            Dean had known Castiel for a few years. He worked in the same office as his mother and they had met at work functions and what not. Dean had always liked looking at Castiel. He was awkward but in a crazy hot way. He had the glasses, the sweaters and that hair that looked like he had just been fucked. Nerdy was definitely a turn on for Dean. But Castiel was an older man who worked with his mom, so he was very much off limits.

            “Hey, Dean?” Mary, Dean’s mother, had stuck her head through his bedroom doorway a few nights ago. “How do you feel about making some extra money?”

            Dean’s father had given him his old 1967 Chevy Impala about six months ago, for his sixteenth birthday. It looked beautiful but the engine needed some work. Since then, he had been working a job at his father’s shop, as well as taking on any random jobs that he could. He wanted to make sure that by the time he left for college, she would be in perfect working order.

            So here Dean was.

            Dean looked at the address on the slip of paper his mother had given him and then back to the large house in front of him. He was not sure what Castiel did at his mother’s company, but he definitely made more money than her, unless his wife was loaded. Taking a deep breath, Dean lightly pounded his fist against the door and waited.

            “Dean,” Castiel opened the door and gave Dean a smile that was all teeth. Dean felt his heart flutter at the sight of it. Not just how he smiled so wide but how he smiled with his entire face, his eyes crinkling up at the sides. “So glad that you made it.”

            “Of course man,” Dean stepped in when Castiel gestured for him to do so. “Anything to make a few extra bucks. Plus, kids are pretty cool.”

            “Jimmy is excited,” Castiel shut the door behind them and then lead Dean further into the house. “His babysitter at his mother’s is a girl who spends most of her time on the phone. He is hoping a boy will spend more time with him. He has all of his video games ready to go. I hope you don’t mind? You are not required to play video games.”

            “I am very open to playing video games,” Dean smiled. This was going to be a piece of cake. If only all of his money could come this easily.

            Castiel spent the next twenty minutes showing Dean around the house. He showed him the kitchen but then gave him thirty bucks to order a few pizzas and some soda for dinner. He then gave him a small list of rules and introduced him to Jimmy. Jimmy was the kid Dean was expecting. He was in love with video games but very smart, definitely the kind of kid you would expect to come from Castiel.

            “I will have my cell phone on me in case you need to reach me,” Castiel lead Dean to a room toward the end of the hall. “I will probably not be home until really late, so if you get tired, you can crash in the spare room.”

            “Sounds good to me,” Dean nodded. He then reassured Castiel that everything would be fine and that he would call him if he needed him. Once he was satisfied, Castiel left Dean to it.

            The rest of the night went by pretty easily. Dean had ordered pizza and Jimmy beat his ass a million times over in Call of Duty. Normally Dean was pretty good at games, but he had not played in a few years, so he was a little rusty. He didn’t mind losing to the kid though, it just made Jimmy happy and that was Dean’s job as a babysitter.

            Ten o’clock came and Dean decided that it would be okay to let Jimmy stay up a little later than Castiel had informed him. It did not last long though and by ten thirty, Jimmy was passed out on the couch. Dean let him sleep for a while, making sure he was fully asleep, before moving him to his bed for the night.

            Once Jimmy was in bed, Dean grabbed himself another soda and settled in to watch some television. Three hundred channels and Dean was watching an infomercial, but hey, he was getting paid to watch that infomercial.

            “Dean,” Dean struggled to pull himself back to reality. It took him a few moments to realize that he was being woken up. He had tried not to fall asleep, but not everyone is successful all the time. “Hello, Dean.”

            Dean looked up at Castiel who was sitting down on the couch beside him. He looked amazing but at the same time, something was off about it. Dean looked a little harder and realized his eyes were red. Had Castiel been crying?

            “Everything okay man?” Dean asked, sitting himself up, wanting to be supportive.

            “Oh yes,” Castiel avoided making eye contact with him. “I will be fine Dean.”

            “You sure?” Dean reached out and placed his hand on Castiel’s thigh. “You can talk to me if you like.”

            “I do not wish to burden you with my problems,” Castiel shook his head at Dean but finally allowed for them to make eye contact.

            “I really would not mind,” Dean reassured him, again and again, until Castiel finally broke down.

            “I went on a date this evening,” Castiel admitted to him. Dean had never really asked what it was that he needed a babysitter for. “It did not go very well.”

            “It was just a date man,” Dean tried to help but he was not very good when it came to relationship stuff. He had told other people, including parts of his family, about his interest in guys. However, it was hard in their town to ever find a guy who was interested back. 

            “And I was horrible at it,” Castiel stood up from the couch. “I have not been with anyone in three years. I finally ask someone out and she gets bored.”

            “How do you know she was bored?” Dean asked seriously.

            “She spent most of her time checking her phone,” Castiel began to pace the living room, obviously working off some of the alcohol in his system. “It was like she was waiting for someone to send her a save message so she could leave. Finally, I asked for a check.”

            “I am sorry man,” Dean rubbed his hands against his thighs, unsure of what to say to this sexy man in front of him. He couldn’t just come out and say how stupid this woman was for not being completely interested in this God of a man.

            “She even elected to take a cab home,” Castiel continued, “couldn’t spend one more minute with me, even if it was to just get home.”

            “Her fucking loss, dude,” Dean finally blurted out. “You are a total catch.”

            “Thank you, Dean,” Castiel stopped and almost smiled, “but you do not need to humor me.”

            “I am not humoring you,” Dean stood up and walked over to Castiel, getting a little closer than he would have liked. He could smell the man in front of him. He smelled the way old books did when you first opened them. Dean had no idea that he liked that smell but it was breathtaking. “I would totally let you drive me home.”

            Castiel did not speak after that. Dean worried that he had said something wrong. Castiel was going to give him some ‘I am flattered’ speech and then send Dean on his way.

            “Really?” Castiel finally spoke and Dean was taken back.

            “Really, really.” Dean smiled at the man in front of him and then took another step toward him.

            “Thank you,” Castiel breathed out, only inches away from Dean now. “I think you should probably …”

            Dean cut him off before he could finish his sentence; the one where he was telling Dean to leave. Dean did not want to leave. He wanted to press his lips against Castiel’s and that is exactly what he did.

            Dean expected Castiel to push him away, but instead, he pulled him closer, wrapping his arms around Dean and holding him against his body. Dean needed to pull back, he needed to breathe but he did not want to break apart from Castiel. He feared that if their lips left one another’s, Castiel would have time to worry about what a horrible idea this was. Castiel was a grown man and Dean was only sixteen years old, he could not possibly want this.

            “Dean,” Castiel finally pulled his lips away but kept his arms wrapped around Dean. “We should not do this.”

            “Why not?” Dean leaned in again and pressed his lips back against Castiel’s, pushing his tongue forward until Castiel opened his mouth and let Dean in.

            “There are so many reasons why we should stop,” Castiel pulled back again to answer but not far enough to break contact.

            “Please,” Dean moaned into Castiel’s mouth. “I want to do this.”

            “But Dean,” Castiel continued to protest.

            “Just,” Dean pushed until the backs of Castiel’s legs were against the couch. He then broke them apart and pushed Castiel down into a sitting position. “At least let me blow you.”

            Castiel’s eyes got wide as he watched Dean drop to his knees in front of him. He opened his mouth to say something but then closed it, giving Dean the go ahead and do as he pleased. Dean smiled at this. He loved when he got what he wanted.

            Dean worked his hands up Castiel’s legs and along his thighs. He rubbed his hand against Castiel’s cock through his slacks, feeling just how hard the older man was for him. Dean continued to rub it with the palm of his hand. Castiel finally gave into his urges and leaned his head back, letting out a deep gravely moan.

            “Oh god,” he cried out, just barely loud enough to hear.

            Dean took this as a good sign and continued forward. Finally, he began to unbuckle his buckle and then unhook his slacks. Dean pulled at the zipper and then pulled his boxers down slightly, leaving him fully clothed with just his cock now out in the open. Dean spent a few moments taking in the site of Castiel’s cock. It was about six inches long, a little longer than Dean’s but thinner than Dean’s. Dean’s may not be the biggest in length but it was definitely a hand full.

            “Amazing,” Dean whispered, hoping that Castiel had heard him but also hoping that he didn’t. Dean did not need Castiel to know how nervous he really was at this moment.

            Dean leaned forward, brushing the tip of his nose up the length of Castiel’s cock until his mouth was at the tip. Pushing a kiss to the tip, Castiel let out another moan, exciting Dean. Dean kissed it again and then slowly slipped the tip into his mouth.

            Dean licked and sucked around the tip which was now dripping with pre-cum, until Castiel began to buck his hips, begging for more with his body and not his words. Dean was not going to deny him what he wanted and began to take more and more of Castiel into his mouth until he could feel Castiel’s cock in the back of his throat.

            Tears welled in Dean’s eyes as he pulled back and then took Castiel’s entire cock into his mouth again, breathing through his nose.

            “Oh Dean,” Castiel cried out in his sex God voice as he grabbed the back of Dean’s head. “Let me fuck that mouth of yours.”

            Dean looked up at Castiel’s blue eyes looking at him with so much lust and Desire. Finally, Dean nodded, giving him the approval that he was seeking. Soon, Castiel was bucking his hips up into Dean’s mouth while holding firmly onto the back of his head. Over and over he pulled himself out and then thrust his cock as far as he could down Dean’s throat without hurting him. Dean moaned around his cock, encouraging him to continue.

            “Oh fuck,” Castiel cried out, letting go of Dean’s head and gripping onto his shoulders. Dean reached out and grabbed Castiel’s hips, taking over, bobbing his head up and down as Castiel came in his mouth.

            Dean groaned at the salty taste. There was too much of it to swallow, though he tried. A small amount of cum breaking free from the sides of his lips and dripping down his chin. He waited until Castiel’s body quit jerking before pulling his mouth off of his cock and kissing the tip one more time.

            “I am going to hell,” Castiel growled, pulling Dean up to him and kissing him hard, then working to lick the cum off of Dean’s chin. “Straight to hell.”


End file.
